Hydrogen Peroxide → HCID 59239528, compound

Participants

Reaction Steps

A solution of (S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-7-(3-methyloxetane-3-carbonyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (jl) (Example 213) (30 mg, 0.061 mmol), borane (0.5 mL of 1.0 M in THF, 0.5 mmol) and THF (1.5 mL) was heated at reflux for 7 h). Further borane (0.3 mL of 1.0 M in THF, 0.3 mmol) was added, and the solution heated at reflux for 15 h. After cooling to rt, sat. NaHCO3 (1 mL) and 3% aq hydrogen peroxide (1 mL) were added and the mixture stirred vigorously for 3 h. The mixture was diluted with 1 N NaOH (20 ml) and extracted with ethyl acetate (3×10 mL). The combined organic phases were washed with brine (1×10 mL) dried over Na2SO4, filtered and concentrated. The residue was purified by RP-HPLC to afford 8 mg (26%) of the title compound as a colorless solid: 1H NMR (400 MHz, MeOD) δ 8.23-8.09 (m, 2H), 7.53-7.36 (m, 2H), 4.29-4.08 (m, 1H), 3.93 (d, J=11.1Hz, 1H), 3.86-3.61 (m, 6H), 3.58-3.45 (m, 1H), 3.24 (q, J=7.2 Hz, 2H), 2.94-2.77 (m, 1H), 2.77-2.68 (m, 3H), 2.49 (s, 2H), 1.32 (t, J=6.2 Hz, 3H), 1.24-1.06 (m, 3H), 0.95 (s, 6H); LC-MS: m/z=+483 (M+H)+.

Provenance & Evidence